EP0567810A1 - Carburants et lubrifiants contenant une N-alkyl amide d'acide carboxylique - Google Patents

Carburants et lubrifiants contenant une N-alkyl amide d'acide carboxylique Download PDF

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Publication number
EP0567810A1
EP0567810A1 EP93105645A EP93105645A EP0567810A1 EP 0567810 A1 EP0567810 A1 EP 0567810A1 EP 93105645 A EP93105645 A EP 93105645A EP 93105645 A EP93105645 A EP 93105645A EP 0567810 A1 EP0567810 A1 EP 0567810A1
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EP
European Patent Office
Prior art keywords
fuels
alkyl
lubricants
compounds
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP93105645A
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German (de)
English (en)
Other versions
EP0567810B1 (fr
Inventor
Juergen Dr. Mohr
Knut Dr. Oppenlaender
Hans Joachim Pander
Rolf Dr. Schneider
Juergen Thomas
Peter Dr. Schreyer
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BASF SE
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BASF SE
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/56—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/03—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/06—Use of additives to fuels or fires for particular purposes for facilitating soot removal
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28—Amides; Imides

Definitions

  • the invention relates to fuels for internal combustion engines and lubricants containing small amounts of N-alkyl carboxamides.
  • the carburetor and intake system of gasoline engines but also injection systems for fuel odorization in gasoline and diesel engines, are increasingly contaminated by contaminants caused by dust particles from the air, unburned hydrocarbon residues from the combustion chamber and the crankshaft ventilation breather led into the carburetor.
  • the first generation of additives could only prevent the formation of deposits in the intake system, but not remove existing deposits, whereas the additives of the second generation can do both ("keep-clean” and "clean-up effect"), and because of their excellent thermal stability, especially in zones of higher temperatures, namely on the inlet valves.
  • the molecular construction principle of fuel detergents can be generalized as a link between polar structures and mostly higher molecular weight, non-polar or lipophilic residues.
  • a reactive polyisobutene is first carbonylated in an oxo synthesis and then hydrogenated in an aminating manner in the presence of ammonia (DE-OS 36 11 230).
  • DE-OS 20 61 057 discloses a process for the preparation of primary amines and of corresponding formamide derivatives and formimino esters, in which, among other things, polyisobutylene is also converted to amines after the so-called "Ritter reaction".
  • the "Ritter reaction” is the conversion of olefins with HCN or nitriles under acidic catalysis to substituted amides, which can be hydrolyzed to amines.
  • the polyisobutylamines produced according to DE-OS 20 61 057 correspond to the compounds according to DE-OS 22 45 918. Their use as detergents in fuels and lubricants is also mentioned in DE-OS 20 61 057. According to this publication, however, it is necessary to hydrolyze the formamides obtained initially by the Ritter reaction. So you get, as in DE-OS 22 45 918 and DE-OS 36 11 230, only in two stages from the olefin to an effective end product.
  • the present invention was therefore based on the object of providing highly effective detergents for fuels and lubricants which, in terms of process engineering, are as simple as possible, i.e. in one step, from which the corresponding olefins can be produced without large amounts of salt load which can no longer be used being obtained.
  • the olefin component for the "Ritter reaction” is preferably a polyisobutene derived from isobutene and 0 to 30% by weight of n-butene and having an average molecular weight between 250 and 5000. Because of the known mechanism of the "Ritter reaction” it is it is not absolutely necessary that the polyisobutene is an ⁇ -olefin.
  • Hydrogen cyanide is preferably used as the nitrile component, i.e. the respective N-polyisobutylformamides are obtained in the reaction which is carried out on the favorably catalyzed sulfuric acid.
  • nitriles e.g. Acetonitrile or benzonitrile, which can be alkyl-substituted, and the sum of the C atoms of the alkyl substituents can be 1 to 8, can be used.
  • the N-alkyl-carboxamides are added to the fuels and lubricants in amounts effective as dergens, in particular they are added to the fuels in amounts of 50 to 5000, preferably 100 to 2000 ppm and lubricating oils in amounts of 0.5 to 10, preferably 1 to 5 wt .-%, based on the lubricating oil, added.
  • the olefins (polyalkylenes) used in the "Ritter reaction" for the preparation of the additives according to the invention are prepared by polymerization of straight-chain or branched monomeric C2-C30-, preferred C2-C6-, in particular C2-C4-olefins, the polymerization being carried out in this way is that the chain termination leads to a double bond (eg by cationic or coordinative polymerization).
  • Monomeric olefins used to prepare the starting component for the "Ritter reaction” are preferably 1-alkenes, in particular propylene, 1-butene, isobutene or mixtures of these olefins.
  • Ethylene is only used in conjunction with comonomers, since pure polyethylene leads to compounds that are not fuel-soluble under normal conditions.
  • the resulting polyalkylenes can be homopolymers or copolymers, each of which has alkyl side chains with 1 to 28, preferably 1 to 4, in particular 1 to 2, carbon atoms.
  • the polyisobutenes which are preferably used as the starting component for the "Ritter reaction” have an average molecular weight of 500 to 5000, in particular 800 to 2000. They are obtained by known methods by cationic polymerization of isobutene, with a double bond in the monomer last incorporated after the polymer chain has been terminated remains (see, for example: DE-OS 27 02 604 and EP-A 0 145 235).
  • the new additives can also be used in combination with other known detergents and dispersants in fuel additive formulations.
  • R is a polybutyl or polyisobutyl radical derived from isobutene and from 0 to 30% by weight of n-butene and R2 is hydrogen, C1-C10-alkyl or C1-C8-aminoalkyl, which also has further C1-C6-alkyl radicals bearing amino groups can be substituted, means to achieve a very good detergent effect.
  • the testing of the products as fuel additives, especially their suitability as valve and carburetor cleaners, is carried out with the help of engine tests, which are carried out in test bench tests 1.2 l Opel Kadett engine according to CEC-F-02-T-79.
  • a solution of 400 g of polyisobutene (average molecular weight 950, iodine number 27.2) in 400 g of cyclohexane is metered into this mixture over the course of 1.5 hours, the temperature being kept at 10 ° to 15 ° C. by cooling, if necessary. The viscous mixture is then stirred at about 15 ° C. for 14 h.
  • the product After removing the cyclohexane in vacuo, the product remains as an almost colorless, viscous oil, the iodine number of which is still 3.8.
  • the nitrogen content is 1.2%, so the yield is approx. 85 to 90%.
EP93105645A 1992-04-25 1993-04-06 Carburants et lubrifiants contenant une N-alkyl amide d'acide carboxylique Expired - Lifetime EP0567810B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4213677 1992-04-25
DE4213677A DE4213677A1 (de) 1992-04-25 1992-04-25 Kraftstoffe und Schmierstoffe, enthaltend N-Alkyl-Carbon-säureamide

Publications (2)

Publication Number Publication Date
EP0567810A1 true EP0567810A1 (fr) 1993-11-03
EP0567810B1 EP0567810B1 (fr) 1996-07-17

Family

ID=6457491

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93105645A Expired - Lifetime EP0567810B1 (fr) 1992-04-25 1993-04-06 Carburants et lubrifiants contenant une N-alkyl amide d'acide carboxylique

Country Status (3)

Country Link
US (1) US5437695A (fr)
EP (1) EP0567810B1 (fr)
DE (2) DE4213677A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0719761A2 (fr) * 1994-12-30 1996-07-03 Chevron Chemical Company Polyalkyle et polyalkényle amides aromatiques et composition de carburant les contenant
EP1177222A1 (fr) * 1999-04-15 2002-02-06 Ferro Corporation Procede d'obtention de monoamines
WO2011107460A1 (fr) 2010-03-02 2011-09-09 Basf Se Copolymères séquencés et leur utilisation
US8673275B2 (en) 2010-03-02 2014-03-18 Basf Se Block copolymers and their use

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5752990A (en) * 1996-03-29 1998-05-19 Exxon Research And Engineering Company Composition and method for reducing combustion chamber deposits, intake valve deposits or both in spark ignition internal combustion engines
DE19645430A1 (de) * 1996-11-04 1998-05-07 Basf Ag Polyolefine und deren funktionalisierte Derivate
US20110218295A1 (en) * 2010-03-02 2011-09-08 Basf Se Anionic associative rheology modifiers

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2061057A1 (de) * 1969-12-12 1971-06-16 Chevron Res Verfahren zur Herstellung von primaeren Aminen sowie von Formamid-Derivaten derselben
US3996024A (en) * 1973-06-22 1976-12-07 Chevron Research Company Fuel composition
DE3611230A1 (de) * 1986-04-04 1987-10-08 Basf Ag Polybutyl- und polyisobutylamine, verfahren zu deren herstellung und diese enthaltende kraft- und schmierstoffzusammensetzungen
US4743389A (en) * 1982-11-30 1988-05-10 Mobil Oil Corporation N-alkyl amides as friction-reducers for lubricants and fuels
EP0355895A2 (fr) * 1988-08-05 1990-02-28 Shell Internationale Researchmaatschappij B.V. Procédé de préparation de dérivés de l'anhydride succinique
EP0476485A1 (fr) * 1990-09-24 1992-03-25 BASF Aktiengesellschaft Polyisobutylaminoalcools et combustibles pour moteurs à combustion interne contenant ces aminoalcools à haut poids moléculaire

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3338967A (en) * 1964-09-17 1967-08-29 Armour & Co Process for preparing secondary-alkyl primary amines from olefins
US3530153A (en) * 1967-08-25 1970-09-22 Armour Ind Chem Co Process for preparing n-monosubstituted secondary-alkyl amides from olefins
US4044039A (en) * 1969-12-12 1977-08-23 Chevron Research Company HCN-olefin adduct using HF
GB1346765A (en) * 1970-06-16 1974-02-13 Shell Int Research Fuel compositions
NL176177C (nl) * 1971-09-21 1985-03-01 Shell Int Research Werkwijze voor de bereiding van aminen geschikt als toevoegsel voor smeermiddelen en brandstoffen.

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2061057A1 (de) * 1969-12-12 1971-06-16 Chevron Res Verfahren zur Herstellung von primaeren Aminen sowie von Formamid-Derivaten derselben
US3996024A (en) * 1973-06-22 1976-12-07 Chevron Research Company Fuel composition
US4743389A (en) * 1982-11-30 1988-05-10 Mobil Oil Corporation N-alkyl amides as friction-reducers for lubricants and fuels
DE3611230A1 (de) * 1986-04-04 1987-10-08 Basf Ag Polybutyl- und polyisobutylamine, verfahren zu deren herstellung und diese enthaltende kraft- und schmierstoffzusammensetzungen
EP0355895A2 (fr) * 1988-08-05 1990-02-28 Shell Internationale Researchmaatschappij B.V. Procédé de préparation de dérivés de l'anhydride succinique
EP0476485A1 (fr) * 1990-09-24 1992-03-25 BASF Aktiengesellschaft Polyisobutylaminoalcools et combustibles pour moteurs à combustion interne contenant ces aminoalcools à haut poids moléculaire

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0719761A2 (fr) * 1994-12-30 1996-07-03 Chevron Chemical Company Polyalkyle et polyalkényle amides aromatiques et composition de carburant les contenant
EP0719761A3 (fr) * 1994-12-30 1996-09-11 Chevron Chem Co Polyalkyle et polyalkényle amides aromatiques et composition de carburant les contenant
EP1177222A1 (fr) * 1999-04-15 2002-02-06 Ferro Corporation Procede d'obtention de monoamines
EP1177222A4 (fr) * 1999-04-15 2003-02-26 Ferro Corp Procede d'obtention de monoamines
WO2011107460A1 (fr) 2010-03-02 2011-09-09 Basf Se Copolymères séquencés et leur utilisation
US8673275B2 (en) 2010-03-02 2014-03-18 Basf Se Block copolymers and their use

Also Published As

Publication number Publication date
DE59303226D1 (de) 1996-08-22
EP0567810B1 (fr) 1996-07-17
US5437695A (en) 1995-08-01
DE4213677A1 (de) 1993-10-28

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